Valdichiana: an insider’s guide to the territory

8 September 2022
Written by The Italy Insider
Insider's Guide

One day a Virtuoso Travel Agent told us: “If you suggest a winery in Tuscany where my clients can go without bumping in to ten other groups of Americans, you will become my favorite insiders”. We took it to the T. In fact, it is enough to move a little from the borders of Chianti to find quiet areas, where hospitality is seriously genuine and local, where good things are not needed to attract tourists but to satisfy those who live there.

An example is the Valdichiana, between Siena and Arezzo. These cultivated hills rich with medieval towns, endless vineyards, hot springs, poetic scenic roads and and cocooning shelters have nothing on its famous neighbour, and here is why.


where to sleep

Villa San Sanino, torrita di siena

Slow, intimate, authentic. This eighteenth century farmhouse was purchased in 1992 by Ubaldo and Laura who restored the property and in 2012 converted it, with the help of their son Giacomo and daughter Bianca, into a family run boutique hotel with just four rooms. More than a hotel, Villa San Sanino feels like home into which the family, who lives on the premises, warmly welcomes you. WEBSITE

hotel in Tuscany
Waking up at Villa San Sanino
Food in Tuscany
Breakfast at Villa San Sanino

where to eat

Cantina Ercolani, montepulciano

Cantina Ercolani, a wine cellar located inside an ancient underground city, can be accessed from its shop. Private tours are organised here: an underground itinerary connects the cellars of seven Renaissance palaces with stops at the ancient oil mill, the stable, the vinsantaia (it’s a room where the sweet wine is made), the cheese room and a part with a museum of instruments of pleasure and torture, and two Etruscan tombs. They produce: Nobile di Montepulciano, the first Italian DOCG born in 88. WEBSITE

Frantoio Buraschi, Montepulciano

Organise a visit with mini oil tasting courses and lunches in the garden or in the kitchen of the mill. The only mill that produces Montepulciano IGP (and also ended up on Gambero Rosso). They also make organic oil. WEBSITE


Would you like to relax with a glass of vino Nobile in front of one of the most poetic landscapes of the world? Make a pit-stop at Idyllium, situated opposite the Monte Amiata. WEBSITE

Podere il Casale, val d’orcia

Also reviewed by the New York Times, this farm produces everything found on the menu: meat, eggs, cheese. Add an incredible view: expect one of the best angles of Val d’Orcia.

Entrance to Cantina Ercolani
Frantoio Buraschi Ph. Proloco Montepulciano


Italian craftsmanship is going through a moment of great revival, with young people who take over the family activities and revolutionise them. In this beautiful corner of Tuscany you will find many wrought iron workshops and laboratories, painting, jewels and leather good stores who produce objects made to last, despite fashion, and created in compliance with people and the territory.

what to see

Tempio di San Biagio, Montepulciano

The Church of SS. Flora and Lucilla

The Church of SS. Flora and Lucilla in Torrita can be considered a small museum. Romanesque church erected in the 13th century, preserves fragments of frescoes and jewels of pictorial art of the Florentine School of the 1400s, of Benvenuto di Giovanni, Taddeo di Bartolo and Bartolo di Fredi. It also houses the bezel marble The blood of the Redeemer attributed to Donatello (1430).

Sant’Antimo Abbey

An ancient abbey inhabited over the centuries by Benedictine monks. Built in the 12th century, is considered one of the masterpieces of medieval architecture. Harmony of the architecture and the refinement of the decorative elements have become an expression of the canon of true beauty.

National Archaeological Museum of Chiusi

It houses Etruscan, Roman and Lombard finds, a journey from Prehistory to the Middle Ages with ceramics, sculptures, ornaments in gold and silver, the canopi of Chiusi, (urns painted and decorated in relief), Etruscan goldsmithing, the grave goods from the Tomb of the Pania, the splendid urns in marble and alabaster. From the Roman period, an exceptional portrait of Augustus and the mosaic with hunting scenes from the villa of Montevenere. From the museum it is possible to reach the necropolis of Poggio Renzo and visit the tombs of Leone, della Pellegrina and those with splendid pictorial representations of the Monkey and Colle Casuccini.


truffle hunting

White truffle season begins, the most prized of all. From 15th September, you can participate in a truffle hunt in the woods of the Valdichiana Senese, guided by an expert tartufaio (this is how we call truffle hunters in Italy). While he narrates some brilliant legends, his Lagotto (truffle dog) explores and sniffs and when he starts wagging his tail and digging near a bush or tree he has almost certainly found the treasure. After the hunt, there is a wine tour in the cellar with private lunch and wine tasting. At the end of the experience, you can buy the truffle you found and bring it at home or have it cooked at Villa San Sanino. WEBSITE


The Valdichiana is famous for its warm sulphurous waters which are a true refreshment for body, mind and soul, while massages and beauty treatments restore strength and shine to both the body and soul.

Bagni San Filippo is a small town in the Val d’Orcia where you can immerse yourself in pools of hot thermal water outdoors. An easy and flat path winds through the woods to the Fosso Bianco, where a stream creates an extensive spa area (free). At the end of the path, the White Whale Waterfall is a large block of limestone where the water cascades with a temperature of up to 48 °, allowing swimming even in the middle of winter.

Wellness has deep roots in this area. At Villa San Sanino you can book a modelling or draining massage with the innovative Brazilian method Renata França, in your suite or in the garden. Find out more here.


You can cycle along the Sentiero della Bonifica, a 62 km flat path that runs along the Canale Maestro della Chiana passing through the lakes of Montepulciano and some of the the most beautiful villages in the area (Chiusi and Cortona, for example) up to Arezzo. Here you will find all the itineraries to do by Bici in Toscana. Another panoramic route is the Sentiero del Nobile, a ring of 300 km (500 m in altitude) that starts from Pienza arrives in Montepulciano and returns to Pienza, crossing the hills of the Val d’Orcia. Focus on the landscape especially in the stage from Rocca di Tentennano to Castiglione d’Orcia.

Truffle Hunt. Ph. Credit Belmond
Bike around Tuscany


Lucciola bella is a serpentine road flanked by cypresses, very close to Montepulciano. (There are also many dirt roads for bucolic walking). Along the way, detour to the Vitaleta Chapel, small and private on the top of a hill: it has become the icon of the Val di Chiana since it was photographed for the cover of National Geographic magazine. You can then return from the Strada del Gladiatore, a scenic route in the Terrapille countryside.


Treno Natura della Val d’Orcia

Take a historic train at Asciano station and enjoy the slow journey up to Monte Antico: 51.2 km through the heart of authentic and rural Tuscany, connecting the lands of Siena and Grosseto. WEBSITE

Stay up to date. Sign up to our newsletter